Sodium hydride → Ethyl 6-amino-9-(2,5-dichlorobenzyl)-9H-beta-carboline-3-carboxylate

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Reaction Steps

A mixture of ethyl 6-amino-9H-β-carboline-3-carboxylate (100 mg, 0.39 mmol), NaH (0.58 mmol, 24 mg of 60 wt. % suspension in mineral oil) and 2,5-dichlorobenzyl chloride (115 mg, 0.59 mmol) in DMF (2 mL), was treated according to Method A. Purification of the crude product by column chromatography on silica with hexane/ethyl acetate (7:3) as eluent furnished the desired product (87 mg, 54% yield) as a yellow solid. 1H NMR (DMSO-d6) δ8.96 (s, 1H), 8.74 (s,1H), 7.60 (d,J=8.6 Hz, 1H), 7.48 (d, 1H), 7.41 (dd, J=8.4 Hz, 2.1Hz, 1H), 7.35 (d, J=8.8 Hz, 1H), 7.01 (d,J=8.6 Hz, 1H), 6.51 (d, J=1.8 Hz, 1H), 5.80 (s, 2H), 5.10 (br s, 1H), 4.37 (q,J=7.0 Hz, 2H), 1.37 (t, J=7.0 Hz, 3H); MS (APCI; (M+H)+) m/z 414.

Provenance & Evidence